2-Nitroimidazole

• CAS: 527-73-1
• Catalog Number: ACM527731-1
• Category: Main Products
• Molecular Weight: 113.07
• Molecular Formula: C3H3N3O2
• Synonyms: 2-Nitro-imidazo
• IUPAC Name: 2-nitro-1H-imidazole
• InChI: InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
• InChI Key: YZEUHQHUFTYLPH-UHFFFAOYSA-N
• Boiling Point: 287 °C (dec.)-lit.
• Melting Point: 287 °C (dec.)-lit.
• Appearance: Dark yellow powder
• Complexity: 99.2
• CompoundIs Canonicalized: Yes
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Deprecated CAS: 116421-32-0, 151223-78-8
• EC Number: 208-425-5
• Exact Mass: 113.022526347g/mol
• Formal Charge: 0
• Heavy Atom Count: 8
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Isotope Atom Count: 0
• LogP: 0.15 (LogP)
• Monoisotopic Mass: 113.022526347g/mol
• NSC Number: 105831
• Rotatable Bond Count: 0
• Topological Polar Surface Area: 74.5Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• UNII: K8E96XL55D
• XLogP3: 0.1

Case Study

2-Nitroimidazole for the Synthesis of 2-(2-(2-Nitro-1H-imidazole-1-yl)ethyl)isoindoline-1,3-dione

Liu W, et al. European Journal of Medicinal Chemistry, 2025, 289, 117443.

The synthesis of 2-(2-(2-nitro-1H-imidazole-1-yl)ethyl)isoindoline-1,3-dione was carried out through a nucleophilic substitution reaction utilizing 2-nitroimidazole as the key reagent. A solution of 2-(2-bromoethyl)isoindoline-1,3-dione (41.8 g, 164.5 mmol) and potassium carbonate (45.5 g, 329 mmol) in N,N-dimethylformamide (DMF, 150 mL) was prepared, to which 2-nitroimidazole (19.2 g, 170 mmol) was added. The reaction mixture was stirred until completion, followed by cooling to room temperature. The solid byproduct was removed via filtration, and the filtrate was subjected to liquid-liquid extraction with ethyl acetate and water. The combined organic layers were sequentially washed with water and saturated brine before drying and solvent removal under reduced pressure. The crude product, obtained along with the filter cake, was purified by silica gel column chromatography using a dichloromethane and ethyl acetate (5:1) eluent system. This method efficiently yields 2-(2-(2-nitro-1H-imidazole-1-yl)ethyl)isoindoline-1,3-dione, demonstrating the practical application of 2-nitroimidazole in heterocyclic compound synthesis.

Synthesis of Dioxalane-Substituted Imidazole Derivatives Using 2-Nitroimidazole

Renault K, et al. European Journal of Organic Chemistry, 2023, 26, e202300307.

2-Nitroimidazole serves as a key intermediate in the synthesis of 1-(2,2-dimethyl[1,3]dioxalan-4-ylmethyl)-2-nitro-1H-imidazole derivatives via the Mitsunobu reaction. In the first step, 2-nitroimidazole (200 mg, 1.77 mmol) was dissolved in dry THF (12 mL) under an argon atmosphere at 0°C. Compound 2 or compound 4 was added in equimolar or excess amounts, followed by triphenylphosphine (929 mg, 3.54 mmol) and DIAD (697 μL, 3.54 mmol) to facilitate nucleophilic substitution. For certain reactions, dibutyltin(IV) oxide (880 mg, 3.54 mmol) was introduced to enhance selectivity. The reaction mixture was stirred overnight at room temperature, ensuring complete conversion. Upon reaction completion, the solvent was evaporated under reduced pressure, and purification was performed via flash column chromatography on silica gel. The final products were obtained as a yellowish oil or a white amorphous powder, depending on the substrate used. These derivatives, synthesized through a well-controlled pathway, demonstrate the utility of 2-nitroimidazole in constructing complex heterocyclic frameworks relevant to pharmaceutical research, including potential applications in hypoxia-targeting agents and radiosensitizers.

Custom Q&A

What is the molecular formula of 2-Nitroimidazole?

The molecular formula of 2-Nitroimidazole is C3H3N3O2.

What are the synonyms of 2-Nitroimidazole?

The synonyms of 2-Nitroimidazole are Azomycin, 2-NITRO-1H-IMIDAZOLE, and nitroimidazole.

What is the molecular weight of 2-Nitroimidazole?

The molecular weight of 2-Nitroimidazole is 113.08 g/mol.

What is the role of 2-Nitroimidazole?

2-Nitroimidazole has a role as an antitubercular agent.

Is 2-Nitroimidazole a natural product?

Yes, 2-Nitroimidazole is a natural product found in Pseudomonas fluorescens.

What is the IUPAC name of 2-Nitroimidazole?

The IUPAC name of 2-Nitroimidazole is 2-nitro-1H-imidazole.

What is the InChI of 2-Nitroimidazole?

The InChI of 2-Nitroimidazole is InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5).

What is the InChIKey of 2-Nitroimidazole?

The InChIKey of 2-Nitroimidazole is YZEUHQHUFTYLPH-UHFFFAOYSA-N.

What is the CAS number of 2-Nitroimidazole?

The CAS number of 2-Nitroimidazole is 527-73-1.

What is the XLogP3 value of 2-Nitroimidazole?

The XLogP3 value of 2-Nitroimidazole is 0.1.

Synthetic Use

Upstream Synthesis Route 1

• 42383-61-9

• 527-73-1

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 17, p. 5102 - 5106

Upstream Synthesis Route 2

• 7720-39-0

• 527-73-1

Reference: [1]Organic Process Research and Development,2014,vol. 18,p. 886 - 890
[2]Organic Mass Spectrometry,1982,vol. 17,p. 299 - 303

Downstream Synthesis Route 1

• 527-73-1

• 7720-39-0

Reference: [1] RSC Advances, 2014, vol. 4, # 43, p. 22567 - 22574
[2] Patent: WO2018/160891, 2018, A1, . Location in patent: Page/Page column 497-498

Downstream Synthesis Route 2

• 527-73-1

• 7720-39-0
• 102998-00-5

Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 14, p. 4308 - 4314

Downstream Synthesis Route 3

• 2508-01-2
• 527-73-1

• 131504-99-9

Reference: [1]Suto, Mark J.; Stier, Michael A.; Werbel, Leslie M.
[Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1207 - 1209]

Downstream Synthesis Route 4

• 527-73-1
• 5455-98-1

• 93272-45-8

Reference: [1]Wang, Feng; Fan, Di; Qian, Jun; Zhang, Zhe; Zhu, Jianhua; Chen, Jian
[Medicinal Chemistry, 2015, vol. 11, # 7, p. 649 - 655]
[2]Ahmed; Stratford; Jenkins
[Arzneimittel-Forschung/Drug Research, 1985, vol. 35, # 12, p. 1763 - 1768]
[3]Current Patent Assignee: BRACCO SPA - US2005/74402, 2005, A1
Location in patent: Page/Page column 6
[4]Current Patent Assignee: BRACCO SPA - US5608110, 1997, A

* For details of the synthesis route, please refer to the original source to ensure accuracy.